Presidential candidate Herman Cain applauds as he waits to speak at the Iowa Faith & Freedom Coalition's Presidential Forum at the Iowa State Fairgrounds in Des Moines, Iowa, Saturday.

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Washington — From the start, Herman Cain has confounded the Republican elite. The former pizza magnate, Navy mathematician, and talk radio host with no political experience jumped into the presidential race with both feet way back in January and has never looked back.

Mr. Cain has enticed GOP voters with his catchy "9-9-9" tax plan and moved them with his up-by-the-bootstraps life story. He has also raised eyebrows with a series of gaffes, strange ads, and reports of "chaos" within his campaign. But he’s a robo-candidate, plowing ahead, ever-smiling. And he’s ahead in the polls among likely GOP primary voters, both nationally and in key early nominating states. His Achilles’ heel is fundraising and organization.

Could Cain actually win the Republican nomination? In theory, yes. But political analysts still view Cain as a long shot.

A story in The New York Times posted Wednesday quotes former aides describing a campaign that churns through staff, mishandles potential donors, and makes nonsensical scheduling decisions. All campaigns, especially those new to presidential politics, go through some disorder, but given that Cain’s argument for the presidency is his private-sector management experience, he has a lot to prove in short order.

But at least one experienced Republican strategist now working for Cain speaks optimistically about Cain’s chances. Steve Grubbs, the new chairman of Cain’s campaign in Iowa, describes an effort that is now on track in this critical early nominating state, with fundraising that is “doing dramatically better” and finally getting volunteers organized. Mr. Grubbs, former chairman of the Iowa GOP who has worked on past presidential campaigns, spoke to the Monitor Wednesday by phone after a meeting with Iowa campaign staff and volunteers.

“The volunteer phone bank was brisk,” said Grubbs. “That’s what I wanted to see. That’s a bit of a change.”

In July, Cain’s top staffers in Iowa resigned, citing a lack of attention by Cain to the state. Grubbs’s appointment as Iowa chairman, announced last Thursday, signaled a renewed commitment by Cain to Iowa, which holds the first nominating contest on Jan. 3. Grubbs says the campaign’s goal is to appoint precinct captains to 80 percent of the state’s 1,800 precincts by Dec. 1.

“So far, we’re exceeding our goals,” says Grubbs, who is unpaid. Cain has four paid staffers in Iowa, he says.

The name of the game in Iowa is organization. Unlike a primary, which involves only voting, an Iowa GOP caucus entails speeches, casting of ballots, party fundraising, and other party business. To do well, a campaign needs to engage in major voter outreach to get supporters to show up on a cold winter night, and devote a fair amount of time. Voter passion matters, but it will take a candidate only so far.

Iowa’s caucuses are only 10 weeks away, and Cain is getting a late start. Still, he’s strong in the polls. The RealClearPolitics average of recent polls in Iowa shows Cain leading among likely Republican caucus-goers with 28 percent, followed by former Massachusetts Gov. Mitt Romney at 23 percent. The latest poll, by CNN, has Cain at 21 and Mr. Romney at 24. If Cain can do well in Iowa, that could open the floodgates of donations and set him up to be a serious contender.

“He has to win Iowa; I think that’s the real key,” says Ford O’Connell, chairman of the conservative Civic Forum PAC. “Should he win Iowa, people will show him how to build a national organization.”

Still, Mr. O’Connell believes it’s “extremely unlikely” that Cain will go on to win the nomination, “given his lack of organization and campaign resources.”

In the third quarter of 2011, Cain raised $2.8 million, versus Romney’s $14 million and Texas Gov. Rick Perry’s $17 million. But Governor Perry has sunk in the polls after a series of sub-par debate performances, and Cain has been the direct beneficiary. He won the Florida straw poll a month ago and has been a top-tier contender ever since, at least in the polls.

Romney is the only candidate who combines good poll numbers, major-league fundraising, and extensive organization. But he seems to have hit a ceiling in national polls in the mid-20s. Whether he can break through that ceiling is an open question. If voters continue to resist him, the question is who will emerge as the “anti-Romney” – and when will that alternative become clear.

Cain is certainly in the running to be the one who goes head-to-head against the establishment-backed Romney, but a lot of analysts are still looking to Governor Perry – who has the more typical résumé for a presidential candidate – to ultimately fill that role.

Cain has plenty of tea party support to fuel his outsider status, though not all tea partyers support him. Some object to his having served as chairman of the Kansas City Federal Reserve Bank earlier in his career; they also didn’t like his favorable comment during the Oct. 11 debate about former Fed Chairman Alan Greenspan.

The real question about Cain is whether he can convince enough voters that he is running a serious campaign – and that his lack of political and policy experience wouldn’t put him at a insurmountable disadvantage against President Obama in the general election.

He recently has committed a series of gaffes that make political observers wonder whether he has given this campaign enough thought to be successful. He calls himself “pro-life,” but then described abortion as a personal “choice” that should not involve the government. Last week, he said he would consider freeing all the prisoners in the Guantánamo Bay prison camp in exchange for a hypothetical US hostage. He didn’t know what “neoconservative” meant in a discussion on foreign policy.

“He’s a tremendously charming, capable guy, but he doesn’t seem to be a serious candidate,” says Dennis Goldford, a political scientist at Drake University in Des Moines, Iowa. “He hasn’t taken the time to build an organization or think through in depth the range of issues and policies he’d have to address.”

Other analysts point to the one commodity Cain has that is lacking in the other candidates: an idea that got people talking, his 9-9-9 tax plan. Perry did raise an impressive sum of money in the third quarter, but the history of campaigns is littered with fundraising stars who go nowhere when the voters have their say.

“The power of an idea in this primary is very important,” says Republican pollster David Winston. “Cain has proven that. Whether his idea will stand up to vetting, we’ll find out.”

Grubbs, Cain’s man in Iowa, maintains that Iowans will be seeing a lot more of Cain in coming weeks. And, he adds, Cain’s book tour, which critics said was distracting from his campaign, is over. “He’s campaigning,” he says.